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How to (Successfully) Travel With a Friend

Have a conversation about your individual travel expectations — everything from how to spend free time to money — to get an idea of your travel compatibility

By Natalia Lusinski

The alarm is blaring BEEP, BEEP, BEEP… My friend, Anne, in the bed next to mine in our hotel room, darts right up, perky as can be.

"Wake up, Nat! It's time to start the day!" she says as she heads to the bathroom.

Two friends traveling abroad together. Next Avenue, traveling with a friend
"You do not need to do everything together. Sometimes, you just need a break or may want to do something you're interested in, but your friend is not. That's okay."  |  Credit: Getty

Did I mention it's 6 am? And we're on vacation? Doesn't "vacation" mean to vacate from our ordinary lives and sleep in?

"You really don't know someone until you've traveled with them."

"If we get ready fast enough, we can be the first ones at breakfast!" Anne continues before the noise of the shower drowns her out.

She and I had never traveled together before, and our wake-up and going-to-bed times were one of many ways we didn't seem compatible, travel-wise. This was Day 1 of our trip. Now what?

6 Dos and Don’ts When Traveling With a Friend 

There are many factors to consider before you travel with a friend. I decided to speak to someone who recently did so, as well as to a travel expert, for their input on how to make a trip with a friend memorable — for all the right reasons, not the wrong ones.

1. Before planning anything, have a talk about your vacation expectations. "I always tell people to go on their honeymoon before they get married," says travel expert John E. DiScala, founder of JohnnyJet.com. "You really don't know someone until you've traveled with them."

And this applies to platonic relationships, too. Do you want to go somewhere where you can party all night? Or more to relax on the beach with a good book? Do you want to be together 24/7? Or have some alone time, too?

"These are all good types of questions to figure out in advance," says DiScala. "It's better to find out when you're still at home than go and have a miserable time."

2. Discuss what you'd like to do on the trip — and be specific. Are you a person who needs structure? Or are you more go-with-the-flow? If you're set on going to a museum that requires you get tickets months in advance, for instance, you'll have to plan accordingly.

"It all depends on what each person likes and how they want to spend their time while on vacation," DiScala says. "Some people love to do something active, like golf, others want to gamble, and others want to go out all night and meet someone. Know your audience — and your audience is the friend you'll be traveling with."

"I think it was a compromise for my friend; some days, she might have been happy to sit in a cafe for a couple of hours."  

Rachelle Jackson, 50, who's based in Los Angeles, inadvertently followed Jet's advice when taking a birthday trip with a friend. "Since I travel so much for work and had been to nearly 100 countries, we agreed to look for something that would be new for me and interesting for us both," she says. "I had never done a cruise before, but she had and picked a cruise line she liked."

To prepare for the trip, they bought some guidebooks and watched several Rick Steves videos to get oriented with the main sites at each of the nine port stops, which included places like Oslo, Norway, Tallinn, Estonia and St. Petersburg, Russia.

"My friend agreed to follow my inclination to do as much as we could each day off the ship, leaning into the idea that we might only ever get one day in each city in our whole lives, so let's make the most of it," Jackson explains.

Each port day, they'd spend the majority of their time off the ship, exploring. "I think it was a compromise for my friend; some days, she might have been happy to sit in a cafe for a couple of hours," says Jackson.   

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3. Remember, it's okay not to spend every waking minute together. "You do not need to do everything together," DiScala says. "Sometimes, you just need a break or may want to do something you're interested in, but your friend is not. That's okay."

On my trip with my friend who liked to wake up at dawn, we eventually compromised and decided I'd sleep in — and we'd start the day together with an early lunch. And if one of us wanted to go to a museum, and the other wanted to wander around town, we'd split up and reconvene later.

"Personally, I would never share a room with someone I was not good friends with."

4. Decide if you'll get separate hotel/Airbnb rooms. DiScala says there are pluses and minuses to sharing a room with a friend. "Share a room if you want to save money and spend more time with the person," he says. "But if you have different habits — like one of you is a morning person or likes to watch TV all night — it may be best to have separate rooms and then meet up the next day. Personally, I would never share a room with someone I was not good friends with."

If you do share a room, setting up boundaries is also important, DiScala says, in case your friend gets in late. And be prepared for little things, too, like if the person snores or opens the blinds first thing in the morning. "Have your eye mask and earplugs ready," he adds.

5. Take a mini trip together first, like a weekend away, before making a longer commitment. If I learned anything from my trip with Anne — aside from talking things out before the trip — it was to take a "test trip" first. Even if you can't spend an entire weekend away with someone before the main trip, spending a whole day together is still helpful, especially if you can manage to have one night away, too.

6. Discuss your budget. DiScala stresses that money is an important topic that must be talked about in advance, no matter how uncomfortable it may be. "If one person has a lot of money to spend and the other does not, things can get awkward — they may not be able to do the same kinds of activities or have the same kind of high-end meals and experiences," he says.

When I traveled with Anne, her company paid for our travel and lodging. We were still responsible for meals. I'd recently been laid off, so we definitely had different price points in mind when it came to eating out and choosing what to do in our free time.

Where to Go on a Trip With a Friend

Now that you know the ins and outs of how to handle traveling with a friend, where should you go?

"Anywhere can be a good friend-trip destination," DiScala says. "It all depends on the main vacation goal and who you're traveling with. Are you both baseball fans and want to go see the Yankees play? Or want to go see Broadway shows in New York City?" He says Palm Springs could be good for golfing or spas, Las Vegas could be good for gambling or night owls, and Iceland could be good for adventure travel or being immersed in nature.

"There is something special about sharing a travel experience and beauty with someone you care about. It can give the memories more depth and meaning."

There are many other things to ask yourselves, too: What type of trip do you want? Hang out on the beach? Go sightseeing? (And how much sightseeing?) Stay in the United States? Go abroad? Travel at peak travel season? Or when it's less crowded, during shoulder season?

DiScala also says to think about your common interests. "Since you are friends, you should already have a good idea of what the person likes and what you like doing together. The key is to base it around the activity (baseball games, spas, etc.) and your travel goal (adventure travel, relaxation, etc.) and go from there."

Jackson agrees, saying, "There is something special about sharing a travel experience and beauty with someone you care about. It can give the memories more depth and meaning."

As for her birthday trip, Jackson says it went well. "I think part of it was because we had set our expectations in advance," she says. "It was a good balance of structure and spontaneity. I find I need the structure to feel I am making the most of my time."

Jackson says she recently traveled with someone who was not into structure as much, which required letting go of a lot of expectations, and especially hope, for seeing a lot of things in the time available.

"As long as you can manage your expectations and understand the travel style of your travel partner, you can have a great trip," she says.

Natalia Lusinski
Natalia Lusinski is a wellness and lifestyle writer and editor, covering everything from health and relationships to travel and personal finance topics. Her work can be seen in several dozen publications, including Business Insider, Yahoo, Forbes, Insight Timer, and the L.A. Times. She spent several years living abroad and is currently working on a travel/grief memoir. More of her writing can be seen in her online portfolio. Offline, she runs a popular pizza Meetup in Los Angeles and is still trying to find her favorite slice. Read More
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